The Best Chicago Sweatshirts for Fall

Chicago Est. 1837 embroidered crewneck sweatshirt with navy thread

Fall is crewneck season. The mornings are crisp, the afternoons are still warm, and a midweight sweatshirt is the only layer you need from the farmers market to the late game. These are our favorite Chicago sweatshirts for fall, and how to pick the one that will get worn the most.

Why an embroidered crewneck

A Chicago sweatshirt is something you will wear for years, so it should age well. Embroidery holds up better than a screen print, and a simple founding-year design never goes out of style. Our embroidered crews are a midweight 50/50 cotton and polyester fleece: warm enough for October along the lakefront, light enough to layer under a coat in November.

1. The Chicago Est. 1837 crew

Home comes first. The Chicago Est. 1837 crew with white thread in Maroon or Forest Green looks made for falling leaves along the lakefront, and Navy, Black, Dark Heather and Military Green are the everyday picks. For a lighter, cleaner look, the navy thread version on Sand or White is the one that goes with everything. The arch and the year are stitched in satin thread across the full chest, so it reads from across the room.

Chicago Est. 1837 embroidered crewneck, navy thread on a white sweatshirt

2. Your neighborhood crew

Chicagoans say Lakeview or Bridgeport before they say Chicago, so this fall we started stitching the neighborhoods too. Each Chicago neighborhood crew carries the neighborhood name in a collegiate arch with CHICAGO and the year it got its start underneath. Try the Logan Square Est. 1836 crew in white thread on Forest Green, the Wicker Park Est. 1870 crew in Chicago-flag red on Sand, or the Pilsen Est. 1875 crew in old gold on Black. Lincoln Park, Lakeview, Bucktown, Bridgeport, Hyde Park, Andersonville, West Loop and Ukrainian Village are live now, with more neighborhoods on the way.

Logan Square Chicago embroidered crewneck, white thread on a navy sweatshirt

3. The Bears retro crew

For Sundays. The Chicago Bears Retro Crewneck is our vintage-style take on the orange and navy, an independent fan design printed on heavyweight fleece. It is the one to wear from the tailgate to the couch, and there are more retro Bears crews, tees and hoodies in the Chicago Bears collection.

Chicago Bears retro crewneck sweatshirt laid flat

4. Chicago Football, Est. 1920

The Chicago Football Crewneck, Est. 1920 is a clean collegiate design for watch parties and cold-weather tailgates. The Chicago Skyline Football Crewneck, 312 puts the skyline and the area code front and center. Both come in youth sizes so the kids can match.

Chicago football crewneck sweatshirt, Est. 1920, in navy

5. Chicago Basketball crews for the long nights

Once the clocks change, hoops season takes over. The Chicago Basketball Crewneck, Est. 1966 is the classic, the Retro 90s crew is for anyone who grew up in that decade, and the Windy City Hoops Crewneck wraps the skyline around the ball.

How to choose thread and color

If you like a darker, richer sweatshirt, pick a white thread crew: Navy, Black, Maroon, Forest Green, Military Green or Dark Heather. For a lighter, cleaner look, pick a navy thread crew on White or Sand. The neighborhood crews add three more threads: Chicago-flag red on White, Sand or Ash, old gold on Navy or Black, and sky blue on Navy or Black. Want it oversized? Go up one size; the size guide photo on every product page has exact measurements.

Match the kids

The Youth Chicago Football Crewneck, the Youth Skyline 312 crew and the Youth Windy City Hoops crew use the same artwork as the adult sizes. Everything for little fans is in Youth & Baby.

Every crew is made to order in the USA and ships free in the U.S. See the whole lineup in Chicago sweatshirts, and if you are shopping ahead for the holidays, start with Gifts Under $50.